I have read everything online about this and am still confused about what is considered "chronically ill" (does a 92 yo who is nearly blind and can't walk or use toilet w/o assistance count?) and how to separate the "medical" part of the assisted living monthly cost from the rest (housing/food). Perhaps there is a tax expert out there who can weigh in as I find the whole thing very confusing. I do understand the way you would deduct it, but not if it would be advisable to do so without triggering an audit. She is self-pay and the payments require she sell securities and will see more capital gains income than in past years.